Basic information
- Standard SMILES
CCCC(N)=O- InChIKey
DNSISZSEWVHGLH-UHFFFAOYSA-N- Molecular formula
- C4H9NO
- Average molar mass
- 87.12 g/mol
- Monoisotopic mass
- 87.06841391
Overview
Butanamide is a monocarboxylic acid amide obtained by formal condensation of butanoic acid and ammonia. It is a primary fatty amide and a member of butanamides.
Names & identifiers
- Preferred name
- Butyramide
- IUPAC
- butanamide
- English name
- Butyramide
- Molecular formula
- C4H9NO
- Molecular weight
- 87.12
Names & synonyms
Show more names
Database identifiers
- CAS
541-35-5- PubChem CID
- 10927
- DTXSID
DTXSID8060248- ChEMBL
CHEMBL1231396- ChEBI
CHEBI:50724- UNII
- 9J6OR937VR
- EC Number
- 208-776-4
- Nikkaji
- J2.639E
Properties
Computed structural properties
- XLogP
- -0.2
- Topological polar surface area
- 43.1 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 2
- Heavy atoms
- 6
- Formal charge
- 0
- Complexity
- 51.5
Experimental & physicochemical properties
LogP
log Kow = -0.21
-0.21
-0.21
Color/Form
Crystals
LEAVES FROM BENZENE
Solubility
Sol in alcohol; slightly sol in ether
INSOL IN BENZENE
In water, 163,000 mg/l @ 15 °C
163 mg/mL at 15 °C
Soluble in water
Boiling Point
216 °C
216.00 to 217.00 °C. @ 760.00 mm Hg
Melting Point
115-116 °C
115 - 116 °C
Vapor Pressure
0.00391 [mmHg]
3.91X10-3 mm Hg @ 25 °C
Physicochemical properties
- Melting point
- 114 · 114-116 °C
- Boiling point
- 216 °C · 216 °C
- Density
- 1.03 · 1.03
- refractive index
- 1.456 · 1.4560
- FEMA
- 4252 · 4252 | BUTYRAMIDE
- Flash point
- 216 °C · 216°C
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- alcohol: soluble(lit.)
- pka
- 16.67 · 16.67±0.40(Predicted)
- form
- powder to crystal
- color
- White to Almost white
- Odor
- 100 % · at 100.00%. nutty
- Water Solubility
- soluble
- Merck
- 14 · 14,1592
- JECFA Number
- 1593 · 1593
- BRN
- 1361528 · 1361528
- Henry's Law Constant
- 3.6 · 3.6×103 mol/(m3Pa) at 25℃, Ebert et al. (2023)
- InChI
- 1S/C4H9NO/c1-2-3-4(5)6/h2-3H2,1H3,(H2,5,6)
- InChIKey
- DNSISZSEWVHGLH-UHFFFAOYSA-N
- SMILES
- CCCC(N)=O
- LogP
- -0.21 · -0.210
- CAS DataBase Reference
- 541 · 541-35-5(CAS DataBase Reference)
- Substances Added to Food (formerly EAFUS)
- BUTYRAMIDE
- FDA UNII
- 9 J6OR937VR · 9J6OR937VR
- NIST Chemistry Reference
- Butanamide(541-35-5)
- EPA Substance Registry System
- Butanamide (541-35-5)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302
- Precautionary statements
- 264 · P264-P270-P301+P312a-P330-P501a
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xn
- Risk Statements
- 22 · 22
- Safety Statements
- 24 · 24/25
- WGK Germany
- 3 · 3
- TSCA
- TSCA listed
- HS Code
- 29241900 · 29241900
- Storage Class
- 13 · 13 - Non Combustible Solids
- Hazardous Substances Data
- 541 · 541-35-5(Hazardous Substances Data)
Safety & regulation
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Butanamide: Does not have an individual approval but may be used under an appropriate group standard
Safety & protection
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.
Toxicology
Interactions
Studies on the effects of antidiuretic hormone (ADH) on diffusion of moderately lipophilic solutes (e.g., butyramide, isobutyramide, & antipyrine, each solute having an oil/water partition > or = 0.0008) across luminal membranes of rabbit cortical collecting tubules, & the effects of ADH on the apparent activation energies (EA, kcal/mol) for water & solute permeation across these tubules revealed that: ADH produced a 60-100% incr in the permeation rates for these solutes, the ADH-dependent apparent EA for water permeation was 9.35 kcal/mol, & the ADH-dependent apparent EA for permeation of moderately lipophilic solutes was in the range 15.8-19.6 kcal/mol. (antidiuretic hormone, Butyramide, Isobutyramide, Antipyrine)
Pyrazole, previously reported to inhibit ethanol oxidation in rats, also effectively blocked the in vivo metab of methanol, propanol, isopropanol, butanol, & isobutanol. Ethanol metab was also inhibited by a variety of oximes & amides, such as butyramide, isobutyramide, acetaldoxime, isobutyraldoxime, & butyraldoxime.
Radioactive tracer & electrolytic techniques were used to study the transport of nonelectrolytes & Na+, respectively, across toad urinary bladders in the presence & absence of antidiuretic hormone (ADH). The permeability of lipophilic mol was roughly proportional to bulk phase oil/water partition coefficients both in the presence & absence of hormone; i.e., ADH elicited a general nonselective incr in the permeation of butyramide & 8 other solutes tested.
Environmental Biodegradation
Bench scale activated sludge assay. Fill and draw operation after 6 hrs 1.3% of theoretical oxygen demand; at 12 hrs 3.8% of theoretical oxygen demand; at 24 hr 6.4% of theoretical oxygen demand.
Reverse osmosis yielded 40.5% rejection from 0.01 M soln.
Non-Human Toxicity Excerpts
Treatment of Pleurodeles waltlii or Triturus helveticus cleaving eggs with 1M formamide resulted in complete destruction of mitotic spindles; centrospheres were blocked; mitotic pyknosis with disappearance of nuclei was observed. Pluripolar mitoses in which asters were separated from spindles occurred in Pleurodeles eggs treated with 0.5M formamide. In a comparative study with acetamide, propionamide, & butyramide, the effect on T. helveticus eggs was observed at smaller concn with increasing number of C atoms in the mol.
Antidote and Emergency Treatment
Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist respirations 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 ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Activated charcoal is not effective ... . Do not attempt to neutralize because of exothermic reaction. Cover skin burns with dry, sterile dressings after decontamination ... . /Organic acids 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 respiratory arrest. Early intubation, at the first sign of upper airway obstruction, may be necessary. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organic acids and related compounds/
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29241900
- risk_code
- 22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 24/25
- Storage Class
- 13 - Non Combustible Solids
- Hazard statements
- H302
- Precautionary statements
- P264-P270-P301+P312a-P330-P501a
- Hazardous Substances Data
- 541-35-5(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Absorption, Distribution and Excretion
Lung endothelial permeabilities were determined by injecting butyramide & other test substances into the jugular vein of anesthetized dogs, followed by analysis of sequential blood samples from the carotid artery. The mathematically derived permeability surface product for butyramide was 42.
Uses & manufacturing
Methods of Manufacturing
Prepn: ...by a modified Willgerodt reaction.
Prepn: ...from butyronitrile.
Prepn: ... from butyryl chloride.
Prepn: ... from butyric acid.
Use Classification
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing Information
Butanamide: ACTIVE
N-BUTYLAMIDE WAS NOT AN EFFECTIVE CRYOPROTECTANT FOR RABBIT SEMEN.
Applications
UsesButyramide was used in the synthesis of hydroxamic acids, electrorheological fluids and β-amodoorganotin compounds. It was used as substrate of (+)-γ-lactamase to develop a microreactor to study enzyme stability, activity, kinetics and substrate specificity.
Preparation methods
PreparationButyramide is prepared by amination of n-butyric acid. n-Butyric acid is heated with ammonia gas bubbled through it, and the reaction mixture reaches 200–215°C after approximately 40 hours. Heating and ammonia flow are then stopped, and the mixture is cooled below 20°C before filtration to yield butyramide.An alternative method involves reacting n-butyric acid with urea: First, heat a mixture of 8 kg of n-butyric acid and 3 kg of urea under reflux for 10 hours. Allow the mixture to cool to 70–80°C, then add a suitable amount of hot ethanol. Decolorize the hot solution, filter it while hot, and cool. The crude product obtained by filtration is recrystallised from ethanol to yield the final product.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Additional notes
DefinitionChEBI: Butanamide is a monocarboxylic acid amide obtained by formal condensation of butanoic acid and ammonia. It is a primary fatty amide and a member of butanamides.
Related reactions
Linked notes
Loading…