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1,3-Phenylenediamine(CAS No. 108-45-2)

1,3-Phenylenediamine C6H8N2 (cas 108-45-2) Molecular Structure

108-45-2 Structure

Identification and Related Records

【Name】
1,3-Phenylenediamine
【Iupac name】
benzene-1,3-diamine
【CAS Registry number】
108-45-2
【Synonyms】
m-Phenylenediamine(8CI)
1,3-Diaminobenzene
1,3-Diaminophenylene
1,3-Phenylenediamine
3-Aminoaniline
C.I. Developer 11
Developer C
Developer H
Developer M
Direct Brown BR
Direct Brown GG
NSC 4776
RT 30H
m-Aminoaniline
m-Benzenediamine
m-Diaminobenzene
N-butyl anhydride
metaphenylene diamine
m-Phenylenediamine
【EINECS(EC#)】
203-584-7
【Molecular Formula】
C6H8N2 (Products with the same molecular formula)
【Molecular Weight】
108.1411
【Inchi】
InChI=1S/C6H8N2/c7-5-2-1-3-6(8)4-5/h1-4H,7-8H2
【InChIKey】
WZCQRUWWHSTZEM-UHFFFAOYSA-N
【Canonical SMILES】
C1=CC(=CC(=C1)N)N
【MOL File】
108-45-2.mol

Chemical and Physical Properties

【Appearance】
Gray to white crystal Melting
【Density】
1.139
【Melting Point】
63-65℃
【Boiling Point】
282-284℃
【Vapour】
0.00321mmHg at 25°C
【Refractive Index】
1.6339
【Flash Point】
175℃
【Water】
350 g/L (25℃)
【Solubilities】
350 g/L (25 oC)
【Color/Form】
WHITE CRYSTALS BECOMING RED ON EXPOSURE TO AIR
Colorless needles
RHOMBIC CRYSTALS FROM ALCOHOL
COLORLESS RHOMBIC NEEDLES
Dark oxidation products /are/ present in compound exposed to moist air.
【Stability】
Unstable in air
【HS Code】
29215119
【Storage temp】
Store in a tightly closed container. Store protected from light. Store in a cool, dry area away from incompatible substances.
【Spectral properties】
INDEX OF REFRACTION: 1.6339 AT 58 DEG C/D
MAX ABSORPTION (CYCLOHEXANE): 240 NM (LOG E= 3.85) SHOULDER; 293 NM (LOG E= 3.42)
IR: 6522 (Sadtler Research Laboratories Prism Collection)
UV: 1813 (Sadtler Research Laboratories Spectral Collection)
NMR: 458 (Varian Associates NMR Spectra Catalogue)
【Computed Properties】
Molecular Weight:108.14112 [g/mol]
Molecular Formula:C6H8N2
XLogP3:-0.3
H-Bond Donor:2
H-Bond Acceptor:2
Rotatable Bond Count:0
Exact Mass:108.068748
MonoIsotopic Mass:108.068748
Topological Polar Surface Area:52
Heavy Atom Count:8
Formal Charge:0
Complexity:64.9
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Donor Count:2
Feature 3D Cation Count:2
Feature 3D Ring Count:1
Effective Rotor Count:0
Conformer Sampling RMSD:0.4
CID Conformer Count:1

Safety and Handling

【Hazard Codes】
T:Toxic
【Risk Statements】
R23/24/25;R36;R40;R43;R50/53
【Safety Statements 】
S28;S36/37;S45;S60;S61
【HazardClass】
6.1
【Safety】
Hazard Codes:T,N
Risk Statements:23/24/25-36-43-50/53-68-40
23/24/25:Toxic by inhalation, in contact with skin and if swallowed
36:Irritating to the eyes
43:May cause sensitization by skin contact
50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment
68:Possible risk of irreversible effects
40:Limited evidence of a carcinogenic effect
Safety Statements:28-36/37-45-60-61-28A
28:After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer)
36/37:Wear suitable protective clothing and gloves
45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
60:This material and/or its container must be disposed of as hazardous waste
61:Avoid release to the environment. Refer to special instructions safety data sheet
RIDADR:UN 1673 6.1/PG 3
WGK Germany:2
HazardClass:6.1
PackingGroup:III
HS Code:29215119
Hazardous Substances Data:108-45-2(Hazardous Substances Data)
【PackingGroup 】
III
【Sensitive】
Air Sensitive
【Skin, Eye, and Respiratory Irritations】
STRONG IRRITANT TO SKIN. TOXIC BY ... INHALATION.
【Transport】
UN 1673
【Fire Potential】
FIRE POINT: 175 DEG C.
Combustible when exposed to heat or flame.
【Formulations/Preparations】
GRADES: TECHNICAL; 99% MIN PURITY.
【DOT Emergency Guidelines】
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Health: TOXIC; inhalation, ingestion, or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. /Phenylenediamines/
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors, and sewers explosion hazards. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. /Phenylenediamines/
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas. /Phenylenediamines/
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Phenylenediamines/
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Evacuation: ... Fire: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. /Phenylenediamines/
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Fire: Small fires: Dry chemical, CO2 or water spray. Large fires: Dry chemical, CO2, alcohol-resistant foam or water spray. Move containers from fire area if you can do it without risk. Dike fire control water for later disposal; do not scatter the material. Fire involving tanks or car/trailer loads: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. /Phenylenediamines/
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Spill or Leak: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. /Phenylenediamines/
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ First Aid: Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim warm and quiet. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. /Phenylenediamines/
【Protective Equipment and Clothing】
STRONG IRRITANT TO SKIN. TOXIC BY ... INHALATION.
【Specification】

Grey crystal granule
Safety Statements:28-36/37-45-60-61-28A
28:After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer)
36/37:Wear suitable protective clothing and gloves
45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
60:This material and/or its container must be disposed of as hazardous waste
61:Avoid release to the environment. Refer to special instructions safety data sheet
【Octanol/Water Partition Coefficient】
log Kow = -0.33
【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Recommendable method: Incineration. Peer-review: (Peer-review conclusions of an IRPTC expert consultation (May 1985))

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

PREPN: PREPARED BY THE REDUCTION OF M-DINITROBENZENE: KUHN, US PATENT 2,768,209 (1956 TO RINGWOOD); FAUST, J PRAKT CHEM 6, 14 (1958); NEILSON ET AL, J CHEM SOC 1962, 371; TALLEE, PELTIER, COMPT REND 259, 400 (1964).
PREPN: REDUCTION OF META-DINITROBENZENE OR NITROANILINE WITH IRON & HYDROCHLORIC ACID. PURIFIED BY CRYSTALLIZATION.
U.S. Imports

(1977) 8.31X10+6 GRAMS (PRINCPL CUSTMS DISTS)
0-135,700 lb (1976-1982)
U.S. Production

(1977) AT LEAST 4.54X10+7 GRAMS
(1983)
Production figures for m-phenylenediamine are not available. ... From an analysis of two of its principle uses ... infer that production for the 1976-1977 time period could have been as high as 6 million pounds.
【Usage】

Manufacture dyes, rubber curing agents, ion exchange resins, decolorizing resins, formaldehyde condensates, resinous polyamides, block polymers, textile fibers, urethanes, petroleum additives, rubber chemicals, in corrosion inhibitors, in photography, as reagent for gold & bromine.

【Sampling Procedures】
META-PHENYLENEDIAMINE IS COLLECTED ON SULFURIC COATED SILICA GEL AS SULFATE SALT. SALT IS THEN RINSED FROM GEL, DIAZOTIZED & THEN COUPLED TO FORM AN AZO DYE WHICH IS MEASURED SPECTROPHOTOMETRICALLY AT 520 NM.
In Air: by aspiration through ethanol ...

Biomedical Effects and Toxicity

【Biomedical Effects and Toxicity】
The absorption of m-phenylenediamine ... through dog skin, was studied by determining its concentration in the blood. ... After the gel containing 1.5 g of m-phenylendiamine had been applied to the skin, the m-phenylenediamine concentration in the blood rose quickly. In one hour, it approached the level which was maintained through /to/ the last hour of the dermal contact. ... Three hours after the m-phenylenediamine had been washed off the skin, no detectable concentration was found in the blood.
After the /dog abdominal/ skin was washed, m-phenylenediamine concentration in the blood was observed to decline more rapidly than was the case with p-phenylenediamine and 2,5-diaminotoluene.
META-PHENYLENEDIAMINE IS EXCRETED RAPIDLY, UNCHANGED, WITH LITTLE ABSORPTION.
. Groups of seven male Wistar rats were dermally exposed for 24 hr to 556 mumol (14)C-meta-phenylenediamine (MPD; 1,3-diaminobenzene) in either aqueous solution (Group 2) or 4% hydrogen peroxide (Group 3). The percutaneous absorption and the amount of non-excreted radioactivity were significantly higher in Group 2 rats. Radioactivity associated with DNA purified from the liver and kidneys was demonstrated. Urine was the principal route of excretion, especially in Group 2 rats. Rats in Group 3 excreted significantly more MPD in the faeces than did Group 2 rats. Urinary excretion of material that constituted two of the peaks in the high-performance liquid chromatogram demonstrated first-order elimination kinetics. ... [Lam HR, Bisgaard HC; Food Chem Toxicol 27 (11): 741-50 (1989)] PubMed Abstract

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 16(SRC), determined from a measured log Kow of -0.33(2) and a recommended regression-derived equation(3), indicates that 1,3-benzenediamine is expected to have very high mobility in soil(SRC). However, anilines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(4,5); therefore, mobility may be much lower in some soils(SRC). Volatilization of 1,3-benzenediamine is not expected to be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 1.3X10-9 atm-cu m/mole(SRC), from its extrapolated vapor pressure, 2.1X10-3 mm Hg(6), and measured water solubility, 2.4X10+5 mg/l(7). 1,3-Benzenediamine is not expected to volatilize from dry soil surfaces based on its extrapolated vapor pressure(6). Limited biodegradation data indicate 1,3-benzenediamine may be resistant to biodegradation in soil; soil microflora did not cleave the benzene ring of 1,3-benzenediamine in 64 days(8).
AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 16(SRC), determined from a measured log Kow of -0.33(2) and a recommended regression-derived equation(3), indicates that 1,3-benzenediamine is not expected to adsorb to suspended solids and sediment in water(SRC). However, aromatic amines are recognized as having a strong affinity to organic carbon, suggesting that this compound may bind strongly to suspended organic material in water(4,5). 1,3-Benzenediamine is not expected to volatilize from water surfaces(3,SRC) based on an estimated Henry's Law constant of 1.3X10-9 atm-cu m/mole(SRC), derived from its extrapolated vapor pressure, 2.1X10-3 mm Hg(6), and measured water solubility, 2.4X10+5 mg/l(7). 1,3-Benzenediamine may exist partially in the ionized form at environmental pH's based on pKa values of 2.65 and 4.88 at 25 deg C(8). Volatilization of the ionized form is not expected to be an important fate process(SRC). According to a classification scheme(9), BCF values of 1.3 to 4.6 and
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,3-benzenediamine, which has an extrapolated vapor pressure of 2.1X10-3 mm Hg at 25 deg C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1,3-benzenediamine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be about 1.9 hours(3,SRC). 1,3-Benzenediamine absorbs light in the environmental spectrum(4), which suggests a potential for direct photolysis in the environment(SRC).

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