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2,4-Diaminoanisole Dihydrochloride

HCID 11975
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Basic information

CAS
614-94-8
Standard SMILES
COc1ccc(N)cc1N.Cl.Cl
InChIKey
FNGHHDCBSVSOOI-UHFFFAOYSA-N
Molecular formula
C7H12Cl2N2O
Average molar mass
211.09 g/mol
Monoisotopic mass
210.0326684

Names & identifiers

Preferred name
2,4-Diaminoanisole Dihydrochloride
IUPAC
4-methoxybenzene-1,3-diamine;dihydrochloride
English name
2,4-Diaminoanisole dihydrochloride
Molecular formula
C7H11ClN2O
Molecular weight
174.63

Names & synonyms

614-94-82,4-Diaminoanisole dihydrochlorideHSDB 6240UNII-4MYJ0JWO6G4MYJ0JWO6G4-METHOXY-1,3-BENZENEDIAMINE DIHYDROCHLORIDENSC 46761,3-Benzenediamine, 4-methoxy-, hydrochloride (1:2)DTXSID1060637NSC-46762,4-DIAMINOANISOLE DIHYDROCHLORIDE [HSDB]RefChem:82272
Show more names
2,4-Diaminoanisole diHCl2,4-Diaminoanisole Dihydrochloride >4-methoxybenzene-1,3-diamine hydrochloride4-methoxy-m-phenylenediammonium dichloride3-benzenediamine,4-methoxy-dihydrochloride4-methoxy-m-phenylenediamindihydrochloride4-methoxy-1,3-benzenediaminedihydrochloride2,4-Diaminoanisole Dihydrochloride, ≥ 99.0%C12192000 2,4-DiaminoanisolEdihydrochloride
DTXCID30430292,4-Diaminoanisole hydrochloride4Methoxy1,3benzenediamine dihydrochloridemPhenylenediamine, 4methoxy, dihydrochloride1,3Benzenediamine, 4methoxy, dihydrochloride691-479-04-methoxybenzene-1,3-diamine dihydrochlorideMFCD00054337

Database identifiers

CAS
614-94-8
PubChem CID
11975
DTXSID
DTXSID1060637
UNII
4MYJ0JWO6G
EC Number
691-479-0

Properties

Computed structural properties

Topological polar surface area
61.3 Ų
Hydrogen bond donors
4
Hydrogen bond acceptors
3
Rotatable bonds
1
Heavy atoms
12
Formal charge
0
Complexity
108

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Amines, Aromatic
Color/FormCrystalline powder
SolubilitySoluble in water
DecompositionWhen heated to decomposition it emits toxic vapors of /nitrogen oxides and hydrogen chloride/.
Physical DescriptionSolid; [HSDB] Brown odorless crystalline solid; [MSDSonline]

Physicochemical properties

storage temp.
Keep in dark place,Inert atmosphere,Room temperature
Water Solubility
Soluble in water
form
powder to crystal
color
White to Light yellow to Dark green
CAS DataBase Reference
614 · 614-94-8(CAS DataBase Reference)
FDA UNII
4 MYJ0JWO6G · 4MYJ0JWO6G
EPA Substance Registry System

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Danger

H302 (11.1%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P318, P321, P330, P332+P317, P337+P317, P362+P364, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 9 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazards SummaryEvidence of mutagenicity; The parent compound and sulfate also exhibited carcinogenic properties in animals; Emergency treatment: Methemoglobinemia; [HSDB] See 2,4-Diaminoanisole.
Special Reports · 1 item

Evidence is given supporting testing of the class of compounds phenylenediamines for their toxic effects on human health and the environment. The results of toxicity testing of 22 compounds are tabulated as are the effects for which testing is being considered for 13 compounds, and the uses or potential uses of 47 phenylenediamines.[United States EPA; Phenylenediamines; Response to Interagency Testing Committee; Fed Regist 47(5): 973 (1982)]

TSCA Requirements · 1 item

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 1,2-Benzenediamine, 4-methoxy-, dihydrochloride is included on this list.

NIOSH Recommendations · 3 items

NIOSH considers 2,4-diaminoanisole (and its salts) to be a potential occupational carcinogens.

NIOSH usually recommends that occupational exposures to carcinogens be limited to the lowest feasible concn.

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

2,4-Diamino(ring-U-14C)anisole 2HCl administered i.p. to rats was excreted chiefly via the urine (79 and 85% of the dose in 24 and 48 h, respectively). The isotope in the feces was 2.1 and 8.9% of the dose at 24 and 48 h. The major metabolic pathway was acetylation of the amine group(s), resulting in 4-acetylamino-2-aminoanisole and 2,4-diacetylaminoanisole. Oxidative pathways yielded 2,4-diacetylaminophenol (O-demethylation), 5-hydroxy-2,4-diacetylaminoanisole (ring hydroxylation) and 2-methoxy-5-(glycolamido)acetanilide or its isomer (omega-oxidation). These major metabolites were excreted in the urine as free and glucuronic acid conjugates.

Absorption, Distribution and Excretion · 1 item

The percutaneous absorption of 2,4-diaminoanisole dihydrochloride by hairless rats was approx 2 times higher than that of 2-(2,4-diaminophenoxy)ethanol dihydrochloride because of its high lipid affinity. The penetration of both compounds through the skin was concentration-dependent and studied by (14)C-labelling.

Uses & manufacturing

Uses · 4 items

Formerly used in dyeing hair and furs until the late 1970s; [HSDB]

Fur Dressing and Dyeing [Category: Industry]

HAIR DYE COUPLER /FORMER USE/

Used extensively in hair dyes and dyeing of furs until the late 1970s.

General Manufacturing Information1,3-Benzenediamine, 4-methoxy-, hydrochloride (1:2): ACTIVE

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Compound notes

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On this pageBasic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
1 · 1,3-Benzenediamine, 4-methoxy-, hydrochloride (1:2) (614-94-8)
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302+H312+H332
Precautionary statements
261 · P261-P264-P270-P271-P280-P301+P312+P330-P302+P352+P312+P362+P364-P304+P340+P312-P501
Risk Statements
36 · 36/37/38
Safety Statements
26 · 26-36/37/39
RTECS
2693000 · ST2693000
TSCA
TSCA listed
HS Code
29222990 · 29222990
Hazardous Substances Data
614 · 614-94-8(Hazardous Substances Data)

NIOSH considers 2,4-diaminoanisole (and its salts) to be a potential occupational carcinogens. Minimize occupational exposure (especially skin exposures).

Hazard Classes and CategoriesAcute Tox. 4 (11.1%)
Hazardous Reactivities and IncompatibilitiesStrong oxidizers.

Safety & protection

Disposal Methods · 1 item

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Preventive Measures · 4 items

The worker should immediately wash the skin when it becomes contaminated.

The worker should wash daily at the end of each work shift, and prior to eating, drinking, smoking, etc.

Work clothing that becomes wet or significantly contaminated should be removed and replaced.

Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.

Personal Protective Equipment (PPE) · 5 items

Wear appropriate personal protective clothing to prevent skin contact.

Wear appropriate eye protection to prevent eye contact.

Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection.

Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. [Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.]

For more Personal Protective Equipment (PPE) (Complete) data for 2,4-DIAMINOANISOLE DIHYDROCHLORIDE (6 total), please visit the HSDB record page.

Immediately Dangerous to Life or Health (IDLH)NIOSH considers 2,4-diaminoanisole (and its salts) to be a potential occupational carcinogen.

Toxicology

Interactions · 1 item

Male Wistar rats were divided into two groups. Rats of group 1 were fed basal powdered diet containing 610 ppm 2,4- diaminoanisole sulfate (DAAS), 46 ppm 4,4'-thiodianiline (TDA) and 200 ppm N,N'-diethylthiourea (DETU) for 52 weeks (DTD treatment). Rats of group 2 were maintained on basal diet throughout the experiment as controls. At 52 weeks all surviving rats were sacrificed and subjected to an autopsy. Thyroid, lungs, stomach, liver, spleen, kidneys, testes and all gross lesions suspected of being a tumor were removed. After DTD treatment, the incidence of thyroid hyperplasia and papillary thyroid carcinoma was 59% (10/17) and 65% (11/17), respectively. Hepatocellular adenoma was induced in 2 of 17 rats (12%). Papillary thyroid carcinoma metastasis was found in the lung of 1 rat. No neoplastic tumors were found in kidney, spleen, stomach and testis tissue. /2,4-diaminoanisole sulfate/

Adverse EffectsMethemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect
Human Toxicity Excerpts/OTHER TOXICITY INFORMATION/ Ingredients found unsafe for use in cosmetics: Ingredient: 4-methoxy-m-phenylenediamine hydrochloride; Safety Concern: carcinogenicity. /From table/
Non-Human Toxicity Excerpts · 5 items

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ The effect of the carcinogenic hair dye component 2,4-diaminoanisole (2,4-DAA) on thyroid and pituitary morphology was studied. Heavy pigmentation of the hypertrophied thyroid epithelium was present when the animals were fed with 2,4-DAA for 6 weeks. Another hair dye component m-phenylenediamine (m-PDA), which lacks the methoxy group, and which is not carcinogenic, prevented the dark pigmentation of the thyroid epithelium caused by 2,4-DAA, but had only a slight effect on the hypertrophy of the gland. In the pituitary gland of 2,4-DAA-fed animals only a few aldehyde fuchsin positive thyrotrope cells were present. When 2,4-DAA and m-PDA were fed simultaneously, the number of hypertrophied chromophobic cells was greatly increased and the aldehyde fuchsin-positive cells were practically absent. /2,4-Diaminoanisole/

/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ Male Wistar rats were divided into two groups. Rats of group 1 were fed basal powdered diet containing 610 ppm 2,4- diaminoanisole sulfate (DAAS), 46 ppm 4,4'-thiodianiline (TDA) and 200 ppm N,N'-diethylthiourea (DETU) for 52 weeks (DTD treatment). Rats of group 2 were maintained on basal diet throughout the experiment as controls. At 52 weeks all surviving rats were sacrificed and subjected to an autopsy. Thyroid, lungs, stomach, liver, spleen, kidneys, testes and all gross lesions suspected of being a tumor were removed. After DTD treatment, the incidence of thyroid hyperplasia and papillary thyroid carcinoma was 59% (10/17) and 65% (11/17), respectively. Hepatocellular adenoma was induced in 2 of 17 rats (12%). Papillary thyroid carcinoma metastasis was found in the lung of 1 rat. No neoplastic tumors were found in kidney, spleen, stomach and testis tissue. /2,4-diaminoanisole sulfate/

/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ A bioassay of technical-grade 2,4-diaminoanisole sulfate ... was conducted using Fischer 344 rats and B6C3F1 mice. 2,4-Diaminoanisole sulfate was administered in the feed ... to groups of 50 male and 50 female animals of each species. The time-weighted average dietary concentrations ... were 0.12 percent ... and 0.5 percent for the ... rats /and/ ...12 and 0.24 percent /for the mice/. After a 78-week period of chemical administration, observation of the rats continued for an additional 29 weeks and observation of the mice continued for an additional 19 weeks. ... In high dose male and female rat groups, the proportion of animals having one or more of the following malignant follicular-cell thyroid tumors: papillary adenocarcinomas, follicular-cell carcinomas, papillary cystadenocarcinomas, or adenocarcinomas NOS, was significantly greater than the proportion in corresponding control groups. For high dose male rats the proportion of animals having either a C-cell adenoma or a C-cell carcinoma was also significantly increased. The incidence of malignant tumors (squamous-cell carcinomas, basal-cell carcinomas, or sebaceous adenocarcinomas) of the skin and its associated glands were significantly increased among high dose rats of both sexes. Among high dose female mice, the combined incidence of thyroid follicular-cell adenomas and carcinomas was significantly increased. Among high dose male mice, the incidence of thyroid follicular-cell adenomas was significantly increased ... /2,4-Diaminoanisole sulfate/

/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ Two experiments were conducted to examine the effects of 2,4-diaminoanisole sulfate (2,4-DAAS) on thyroid function and carcinogenesis in male Wistar rats. In experiment 1, feeding with 2,4-DAAS resulted in significantly elevated levels of thyroid stimulating hormone (TSH), reduced thyroxine (T4) and triiodothyronine (T3) in the serum, although the latter had almost recovered to normal levels by week 6. However, skin application did not affect serum levels. In experiment 2, administration of 0.5% 2,4-DAAS in the diet for 19 weeks, a week after a single 210 mg/100 g body weight i.p. injection of N-bis(2-hydroxypropyl)nitrosamine (DHPN), significantly increased the incidence and numbers of preneoplastic lesions (focal hyperplasia), adenomas and carcinomas developing in the thyroid gland. Histologically, brown pigment was usually observed within follicular epithelial cells in non-tumoros regions, but not in the tumors themselves. /2,4-diaminoanisole sulfate/

For more Non-Human Toxicity Excerpts (Complete) data for 2,4-DIAMINOANISOLE DIHYDROCHLORIDE (10 total), please visit the HSDB record page.

Evidence for Carcinogenicity · 1 item

Evaluation: There is inadequate evidence in humans for the carcinogenicity of 2,4-diaminoanisole. There is sufficient evidence in experimental animals for the carcinogenicity of 2,4-diaminoanisole. Overall evaluation: 2,4-Diaminoanisole is possibly carcinogenic to humans (Group 2B). /2,4-Diaminoanisole and its salts/

Antidote and Emergency Treatment · 2 items

Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mg/kg up to 200 ml of water for dilution if the patent can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . Cover skin burns with dry sterile dressings after decontamination ... . /Organic bases/Amines and related compounds/

Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. If patient is unresponsive to these measures, vasopressors may be helpful. Watch for signs of fluid overload ... . Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organic bases/Amines and related compounds/

Regulatory information

TSCA Requirements · 1 item

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 1,2-Benzenediamine, 4-methoxy-, dihydrochloride is included on this list.

Safety data

tsca
TSCA listed
rtecs
ST2693000
hs_code
29222990
risk_code
36/37/38
Signal word
Warning
Symbol(GHS)
GHS07
safety_code
26-36/37/39
Hazard statements
H302+H312+H332
Precautionary statements
P261-P264-P270-P271-P280-P301+P312+P330-P302+P352+P312+P362+P364-P304+P340+P312-P501
Hazardous Substances Data
614-94-8(Hazardous Substances Data)