Basic information
- CAS
100-10-7- Standard SMILES
CN(C)c1ccc(C=O)cc1- InChIKey
BGNGWHSBYQYVRX-UHFFFAOYSA-N- Molecular formula
- C9H11NO
- Average molar mass
- 149.19 g/mol
- Monoisotopic mass
- 149.08406397
Overview
4-(dimethylamino)benzaldehyde is a member of the class of benzaldehydes that is benzaldehyde carrying a dimethylamino substituent at position 4. Used as an indicator for detection of indoles and hydrazine. It has a role as a chromogenic compound. It is a member of benzaldehydes, a substituted aniline and a tertiary amino compound.
Names & identifiers
- Preferred name
- 4-(Dimethylamino)Benzaldehyde
- IUPAC
- 4-(dimethylamino)benzaldehyde
- English name
- 4-Dimethylaminobenzaldehyde
- Molecular formula
- C9H11NO
- Molecular weight
- 149.19
Names & synonyms
4-(DIMETHYLAMINO)BENZALDEHYDE100-10-74-Dimethylaminobenzaldehydep-DimethylaminobenzaldehydeEhrlich's reagentBenzaldehyde, 4-(dimethylamino)-p-Formyldimethylanilinep-(Dimethylamino)benzaldehydep-Formyl-N,N-dimethylaniline4-DimethylaminobenzenecarbonalN,N-Dimethyl-p-aminobenzaldehydeReagens ehrlichovo
Show more names
DIMETHYLAMINOBENZALDEHYDEp-DABpara-Dimethylaminobenzaldehyde4-Dimethylaminobenzaldehyde 、p-DimethylaminobenzaldehydeEhrlichsNSC 5517D2004-100G
p-(N,N-Dimethylamino)benzaldehydeDTXSID5021835V7E88PR1YBNSC-5517DTXCID601835CHEBI:91114RefChem:97438202-819-0
Database identifiers
- CAS
100-10-7- PubChem CID
- 7479
- DTXSID
DTXSID5021835- ChEMBL
CHEMBL3188333- ChEBI
CHEBI:91114- UNII
- V7E88PR1YB
- EC Number
- 202-819-0
- Nikkaji
- J4.002I
Properties
Computed structural properties
- XLogP
- 1.8
- Topological polar surface area
- 20.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 2
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 126
Experimental & physicochemical properties
Chemical ClassesNitrogen Compounds -> Other Aromatics (Nitrogen)
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
Melting Point74 °C
Physical Description
Dry Powder
Solid; Unless extremely pure is lemon-colored possibly turning pink on light exposure; [Merck Index] White crystalline solid; May be discolored by light and air; [Sigma-Aldrich MSDS]
Collision Cross Section129.0 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID5021835]
Physicochemical properties
- Melting point
- 72 · 72-75 °C(lit.)
- Boiling point
- 176 · 176-177 °C (17 mmHg)
- Density
- 1.1 g/mL · 1.10 g/mL at 20 °C
- bulk density
- 350 kg/m3 · 350kg/m3
- vapor pressure
- 0.1 hPa · <0.1 hPa (20 °C)
- refractive index
- 20 · n20/D 1.417
- Flash point
- 164 °C · 164 °C
- storage temp.
- 2 · 2-8°C
- solubility
- alcohol: passes test (APHA ≤60)
- pka
- 1 · pK1:1.647(+1) (25°C)
- form
- Liquid
- color
- White to pale yellow
- Odor
- Characteristic odor
- Water Solubility
- 0.3 g/L · 0.3 g/L (20 ºC)
- Sensitive
- Air Sensitive
- λmax
- 385 nm · 385 nm
- Merck
- 14 · 14,3230
- BRN
- 606802 · 606802
- Stability
- Stable, but light sensitive. Incompatible with bases, strong oxidizing agents.
- InChI
- 1S/C9H11NO/c1-10(2)9-5-3-8(7-11)4-6-9/h3-7H,1-2H3
- InChIKey
- BGNGWHSBYQYVRX-UHFFFAOYSA-N
- SMILES
- CN(C)c1ccc(C=O)cc1
- LogP
- 1.81 · 1.810
- CAS DataBase Reference
- 100 · 100-10-7(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 7 E88PR1YB · V7E88PR1YB
- NIST Chemistry Reference
- 4 · Benzaldehyde, 4-(dimethylamino)-(100-10-7)
- EPA Substance Registry System
- 4 · Benzaldehyde, 4-(dimethylamino)- (100-10-7)
- UNSPSC Code
- 41171621 · 41171621
- NACRES
- 85 · NA.85
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 317 · H317
- Precautionary statements
- 261 · P261-P272-P280-P302+P352-P333+P313-P362+P364
- Hazard Codes
- C,Xn,Xi,F
- Risk Statements
- 36 · 36/37/38-52/53-22-67-41-37/38-10-66-37-34-20-20/21/22-36-11
- Safety Statements
- 7 · 7-16-24/25-26-61-45-39-36/37/39-36
- RIDADR
- 2920 · UN 2920 8/PG 2
- WGK Germany
- 1 · 1
- RTECS
- 5775000 · CU5775000
- F
- 8 · 8
- Autoignition Temperature
- 445 °C · 445 °C
- TSCA
- TSCA listed
- HazardClass
- 3 · 3, 6.1,8
- HS Code
- 29223900 · 29223900
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 1 B · Skin Sens. 1B
- Toxicity
- 50 orally · LD50 orally in Rabbit: > 6400 mg/kg
- REACH Registrations
- Active
- Limited Quantities
- 1 L · 1.0 L (0.3 gallon) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 7.4% (11 of 148) of reports.
Warning
H317 (72.3%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P261, P264+P265, P272, P273, P280, P302+P352, P305+P351+P338, P321, P333+P317, P337+P317, P362+P364, P391, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 148 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Benzaldehyde, 4-(dimethylamino)-
Benzaldehyde, 4-(dimethylamino)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzaldehyde, 4-(dimethylamino)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 11-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/21755
p-Dimethylaminobenzaldehyde: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryCauses general anesthesia, somnolence, and ataxia in oral and intraperitoneal lethal-dose studies of mice; [RTECS] May cause irritation; [Sigma-Aldrich MSDS] See Benzaldehyde and N,N-Dimethyl-p-toluidine.
Hazard Classes and CategoriesSkin Sens. 1 (72.3%)
Safety & protection
Protective Action Criteria (PAC)
3.7 [mg/m3]
41 [mg/m3]
250 [mg/m3]
Toxicology
Adverse EffectsNeurotoxin - Other CNS neurotoxin
Safety data
- F
- 8
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- CU5775000
- ridadr
- UN 2920 8/PG 2
- hs_code
- 29223900
- Toxicity
- LD50 orally in Rabbit: > 6400 mg/kg
- risk_code
- 36/37/38-52/53-22-67-41-37/38-10-66-37-34-20-20/21/22-36-11
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- C,Xn,Xi,F
- safety_code
- 7-16-24/25-26-61-45-39-36/37/39-36
- hazard_class
- 3, 6.1,8
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H317
- Limited Quantities
- 1.0 L (0.3 gallon) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
- REACH Registrations
- Active
- Hazard Classifications
- Skin Sens. 1B
- Autoignition Temperature
- 445 °C
- Precautionary statements
- P261-P272-P280-P302+P352-P333+P313-P362+P364
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant & Hackh's Chemical Dictionary, 5th ed, p301, p499)
Uses & manufacturing
UsesUsed as a reagent and to make dyes; [Merck Index]
U.S. Production2023: 2,866 lb
Industry UsesDye
General Manufacturing Information
Synthetic Dye and Pigment Manufacturing
Benzaldehyde, 4-(dimethylamino)-: ACTIVE
Applications
Uses4-Dimethylaminobenzaldehyde is used to prepare colorful Schiff base adducts with amines, pyrroles and indoles. It is often used in the Ehrlich reaction, test for the presence of indoles in a sample containing alkaloids and determination of hydrazine.
UsesIn the presence of oxygen, some bacteria, like E.coli, are able to split tryptophan into indole and alpha-aminopropionic acid. This reagent is for detecting the indole and identify the indole-positive and indole-negative microorganisms.
UsesForms colored condensation products (Schiff bases) with pyrroles1 and primary amines.2
UsesIn the presence of oxygen, some bacteria, like E. coli, are able to split tryptophan into indole and α-aminopropionic acid. This reagent is for detecting the indole and identifying the indole-positive and indole-negative microorganisms.
Uses4-(Dimethylamino)benzaldehyde is used in Ehrlich's reagent for spectrophotometric determination of hydrazine as it reacts to form azo dyes. 4-(Dimethylamino)benzaldehyde is used for determination of u rine bilirubin and porphobilinogen.
UsesUsed as derivitizing agent.
General DescriptionKovac′s reagent for indoles is a solution of 4-(dimethylamino)benzaldehyde and hydrochloric acid in n-butanol.
Upstream & downstream products
Upstream raw materials
Downstream products
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Additional notes
Definition4-Dimethylaminobenzaldehyde is a mamber of the class of benzaldehydes carrying a dimethylamino substituent at position 4. Used as an indicator for detection of indoles and hydrazine.
Related reactions
289 records
Compound notes
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