Product Name

  • Name

    Ethambutol

  • EINECS 200-810-6
  • CAS No. 74-55-5
  • Article Data11
  • CAS DataBase
  • Density 0.987 g/cm3
  • Solubility Soluble in water. Also soluble in chloroform and methylene chloride
  • Melting Point 199 - 204oC
  • Formula C10H24N2O2
  • Boiling Point 345.342 °C at 760 mmHg
  • Molecular Weight 204.313
  • Flash Point 113.661 °C
  • Transport Information
  • Appearance white crystalline hygroscopic powder
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 74-55-5 (Ethambutol)
  • Hazard Symbols
  • Synonyms 1-Butanol,2,2'-(1,2-ethanediyldiimino)bis-, [S-(R*,R*)]-;1-Butanol,2,2'-(ethylenediimino)di-, (+)- (8CI);(+)-Ethambutol;(+)-N,N'-Bis[1-(hydroxymethyl)propyl]ethylenediamine;(+)-S,S-Ethambutol;(2S,7S)-2,7-Diethyl-3,6-diazaoctane-1,8-diol;(S,S)-Ethambutol;Diambutol;EMB;Purderal;d-2,2'-(Ethylenediimino)bis(1-butanol);d-2,2'-(Ethylenediimino)di-1-butanol;d-Ethambutol;d-N,N'-Bis(1-hydroxymethylpropyl)ethylenediamine;
  • PSA 64.52000
  • LogP 0.48920

Synthetic route

(S)-2-aminobutan-1-ol
5856-62-2

(S)-2-aminobutan-1-ol

1,2-dichloro-ethane
107-06-2

1,2-dichloro-ethane

ethambutol
74-55-5

ethambutol

Conditions
ConditionsYield
In ethanol at 78 - 80℃; for 9.5h; Solvent; Temperature;98.01%
(heating);
C12H20N2O4

C12H20N2O4

ethambutol
74-55-5

ethambutol

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 10h; Reflux;91%
(S,S)-N1,N2-bis(1-tert-butyldimethylsilyloxybutan-3-yl)oxamide
909567-52-8

(S,S)-N1,N2-bis(1-tert-butyldimethylsilyloxybutan-3-yl)oxamide

ethambutol
74-55-5

ethambutol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran for 24h; Heating;80%
(S,S)-2-[[[1-(methoxycarbonyl)propylamino]oxalyl]amino]butyric acid methyl ester

(S,S)-2-[[[1-(methoxycarbonyl)propylamino]oxalyl]amino]butyric acid methyl ester

ethambutol
74-55-5

ethambutol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran Heating;75%
Stage #1: (S,S)-2-[[[1-(methoxycarbonyl)propylamino]oxalyl]amino]butyric acid methyl ester With lithium aluminium tetrahydride In tetrahydrofuran for 48h; Heating / reflux;
Stage #2: With sodium hydroxide In tetrahydrofuran; water at 20℃; for 0.5h;		36%
2,2'-bis(4-ethyloxazoline)
36697-75-3

2,2'-bis(4-ethyloxazoline)

ethambutol
74-55-5

ethambutol

Conditions
ConditionsYield
With hydrogen; rhodium(IV) oxide; platinum In ethanol Ambient temperature;
(S)-2-aminobutan-1-ol
5856-62-2

(S)-2-aminobutan-1-ol

ethylene dibromide
106-93-4

ethylene dibromide

ethambutol
74-55-5

ethambutol

Conditions
ConditionsYield
With potassium hydroxide
(4S,4'S)-4,4'-Diethyl-[2,2']bioxazolidinyl

(4S,4'S)-4,4'-Diethyl-[2,2']bioxazolidinyl

ethambutol
74-55-5

ethambutol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether Heating;
(-)-(S)-N,N'-Bis-(2-hydroxy-1-aethyl-aethyl)-oxalsaeurediamid
61051-11-4

(-)-(S)-N,N'-Bis-(2-hydroxy-1-aethyl-aethyl)-oxalsaeurediamid

ethambutol
74-55-5

ethambutol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether
Multi-step reaction with 3 steps
1: SOCl2
2: NaOH / methanol / 1 h / Heating
3: H2 / Pt-RhO2 / ethanol / Ambient temperature
View Scheme
N,N'-bis-(1-benzyloxymethyl-propyl)-ethane-1,2-diamine

N,N'-bis-(1-benzyloxymethyl-propyl)-ethane-1,2-diamine

ethambutol
74-55-5

ethambutol

Conditions
ConditionsYield
With hydrogenchloride; hydrogen; 3percent Pd/C In methanol at 20℃; under 760.051 Torr; for 48h; Hydrogenolysis;
(S,S)-2-[[[1-(methoxycarbonyl)-3-(methylsulfanyl)propylamino]oxalyl]amino]-4-(methylsulfanyl)butyric acid methyl ester
147315-16-0

(S,S)-2-[[[1-(methoxycarbonyl)-3-(methylsulfanyl)propylamino]oxalyl]amino]-4-(methylsulfanyl)butyric acid methyl ester

ethambutol
74-55-5

ethambutol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 64 percent / W-4 Raney nickel / methanol; H2O / Heating
2: 75 percent / lithium aluminum hydride / tetrahydrofuran / Heating
View Scheme
(2S,2'S)-(ethylenediimino)-bis(3-buten-1-yl)benzyl ether
288402-24-4

(2S,2'S)-(ethylenediimino)-bis(3-buten-1-yl)benzyl ether

ethambutol
74-55-5

ethambutol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2 / 3percent Pd/C / methanol / 12 h / 20 °C / 760.05 Torr
2: H2; HCl / 3percent Pd/C / methanol / 48 h / 20 °C / 760.05 Torr
View Scheme
(2S,2'S)-(oxalamido)-bis(3-buten-1-yl)benzyl ether
288402-23-3

(2S,2'S)-(oxalamido)-bis(3-buten-1-yl)benzyl ether

ethambutol
74-55-5

ethambutol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 78 percent / Red-Al / toluene / 20 h / 45 °C
2: H2 / 3percent Pd/C / methanol / 12 h / 20 °C / 760.05 Torr
3: H2; HCl / 3percent Pd/C / methanol / 48 h / 20 °C / 760.05 Torr
View Scheme
N,N'-bis-((S)-1-chloromethyl-propyl)-oxalamide
61051-15-8

N,N'-bis-((S)-1-chloromethyl-propyl)-oxalamide

ethambutol
74-55-5

ethambutol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaOH / methanol / 1 h / Heating
2: H2 / Pt-RhO2 / ethanol / Ambient temperature
View Scheme
CL 40881

CL 40881

ethambutol
74-55-5

ethambutol

Conditions
ConditionsYield
With sodium hydroxide In water
ethambutol
74-55-5

ethambutol

CL 40881

CL 40881

Conditions
ConditionsYield
With hydrogenchloride In ethanol at 65℃; pH=1.3; pH-value;96.3%
ethambutol
74-55-5

ethambutol

aspirin
50-78-2

aspirin

C19H30N2O5

C19H30N2O5

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dimethyl sulfoxide at 30℃; Temperature;96%
calcium carbide
75-20-7

calcium carbide

ethambutol
74-55-5

ethambutol

N1,N2-bis[(S)-1-(vinyloxy)butan-2-yl]ethane-1,2-diamine

N1,N2-bis[(S)-1-(vinyloxy)butan-2-yl]ethane-1,2-diamine

Conditions
ConditionsYield
With potassium fluoride; potassium tert-butylate; water In dimethyl sulfoxide at 130℃; for 3h; Sealed tube;95%
calcium carbide
75-20-7

calcium carbide

ethambutol
74-55-5

ethambutol

N1,N2-bis[(S)-1-(trideuterovinyloxy)butan-2-yl]ethane-1,2-diamine

N1,N2-bis[(S)-1-(trideuterovinyloxy)butan-2-yl]ethane-1,2-diamine

Conditions
ConditionsYield
With potassium fluoride; dimethylsulfoxide-d6; potassium tert-butylate; water-d2 at 130℃; for 3h; Sealed tube;95%
ethambutol
74-55-5

ethambutol

(4S,9S)-4,9-diethyl-2,11-dioxa-5,8-diaza-1λ5-phosphatricyclo[6.3.0.01.5]undecane

(4S,9S)-4,9-diethyl-2,11-dioxa-5,8-diaza-1λ5-phosphatricyclo[6.3.0.01.5]undecane

Conditions
ConditionsYield
With hexaethylphosphoric triamide In toluene for 1h; Condensation; Heating;81%
dichlorobis(dimethyl sulfoxide)platinum(II)

dichlorobis(dimethyl sulfoxide)platinum(II)

ethambutol
74-55-5

ethambutol

{PtCl2(S,S-N,N'-bis(1-hydroxy-2-butyl)ethylenediamine)}

{PtCl2(S,S-N,N'-bis(1-hydroxy-2-butyl)ethylenediamine)}

Conditions
ConditionsYield
With lithium chloride In methanol according Wilkinson, Shepard, Thomas, Baughn J. Am. Chem. Soc., 1961, 83, 2212-2214; Wilkinson, Cantrall, Shepard, J. Med. Pharm. Chem., 1962, 835-845; Grandi, Farmaco, 1969, 24, 490-495; Pt-complex and amine treated with aq. LiCl; 80°C, 5 h;; elem. anal.;;80%

Ethambutol Chemical Properties

IUPAC Name: (2S)-2-[2-[[(2S)-1-hydroxybutan-2-yl]amino]ethylamino]butan-1-ol
Synonyms: Ethambutol;(+)-2,2-(Ethylenediimino)di-1-butanol ; (+)-2,2’-(Ethylenediimino)Di-1-butanol;(+)-n,n’-bis(1-(hydroxymethyl)propyl)ethylenediamine ; (+)-S,s-ethambutol ;(R)-2,2’-(1,2-ethanediyldiimino)Bis-1-butanol ; 2,2’-(1,2-Ethanediyldiimino)bis-,(r-(r*,r*))-1-butano ; 2’-(1,2-Ethanediyldiimino)bis-(r)-1-butano
CAS: 74-55-5
MF: C10H24N2O2
MW: 204.31
MS:
EINECS: 200-810-6
Mol File: 74-55-5.mol
Surface Tension: 38 dyne/cm 
Density: 0.987 g/cm3 
Flash Point: 113.7 °C 
Enthalpy of Vaporization: 68.26 kJ/mol 
Boiling Point: 345.3 °C at 760 mmHg
Flash Point: 95°C  
Vapour Pressure: 3.9E-06 mmHg at 25°C
eat Of Vaporization:49.0 kJ/mol
Refractive Index:1.5738 (20 C)

Ethambutol Uses

Tibutol (74-55-5) has anti-tuberculosis effect on the common tuberculos iof anti-TB drug resistance . the product can still have inhibitation,but It's inhibitory effect is weaker than the small isoniazid,  approximation with streptomycin.no effect on other bacteria and fungi.

Ethambutol Toxicity Data With Reference

Organism

Test Type

Route

Reported Dose (Normalized Dose)

Effect

Source

human

TDLo

oral

1410mg/kg/11W (1410mg/kg)

sense organs and special senses: visual field changes: eye

New Zealand Medical Journal. Vol. 111, Pg. 428, 1998.

mammal (species unspecified)

LD50

intravenous

350mg/kg (350mg/kg)

lungs, thorax, or respiration: other changes

Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 63(3), Pg. 114S, 1967.

mammal (species unspecified)

LD50

subcutaneous

890mg/kg (890mg/kg)

lungs, thorax, or respiration: other changes

Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 63(3), Pg. 114S, 1967.

man

TDLo

oral

332mg/kg/31D- (332mg/kg)

lungs, thorax, or respiration: "fibrosis, focal (pneumoconiosis)"
blood: eosinophilia

Journal of Allergy and Clinical Immunology. Vol. 100, Pg. 712, 1997.

man

TDLo

oral

600mg/kg (600mg/kg)

peripheral nerve and sensation: structural change in nerve or sheath
behavioral: changes in motor activity (specific assay)
kidney, ureter, and bladder: other changes in urine composition

British Medical Journal. Vol. 2, Pg. 1105, 1976.

man

TDLo

oral

1200mg/kg (1200mg/kg)

skin and appendages (skin): "dermatitis, other: after systemic exposure"

British Medical Journal. Vol. 2, Pg. 1105, 1976.

mouse

LD50

intraperitoneal

1075mg/kg (1075mg/kg)

behavioral: convulsions or effect on seizure threshold

Dissertationes Pharmaceuticae et Pharmacologicae. Vol. 23, Pg. 463, 1971.

mouse

LD50

intravenous

240mg/kg (240mg/kg)

behavioral: convulsions or effect on seizure threshold

Dissertationes Pharmaceuticae et Pharmacologicae. Vol. 23, Pg. 463, 1971.

mouse

LD50

oral

8700mg/kg (8700mg/kg)

behavioral: convulsions or effect on seizure threshold

Dissertationes Pharmaceuticae et Pharmacologicae. Vol. 23, Pg. 463, 1971.

rat

LD50

oral

998mg/kg (998mg/kg)

 

Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 9, Pg. 759, 1967.

women

TDLo

oral

900mg/kg/60D- (900mg/kg)

liver: "jaundice, cholestatic"

British Medical Journal. Vol. 292, Pg. 866, 1986.

Ethambutol Safety Profile

http://www.chemicalbook.com/

http://www.chemspider.com/Chemical-Structure.3164.html

http://chem.sis.nlm.nih.gov/

http://pubchem.ncbi.nlm.nih.gov/

http://www.google.com/

Ethambutol Specification

Ingestion:If Tibutol (74-55-5) is swallowed, wash out mouth with water provided person is conscious. Call a physician.
Inhalation:If inhaled, remove to fresh air. If not breathing give artificial respiration. If breathing is difficult, give oxygen.
Eyes:Assure adequate flushing of the eyes by separating the eyelids with fingers.
Handling and Storage Back to Contents
Storage:Keep tightly closed. Store Tibutol (74-55-5) at 2-8 °C.
Personal Protection:Wear appropriate government approved respirator, chemical-resistant gloves, safety goggles, other protective clothing. Faceshield (8-inch minimum).
Exposure Effects:Irritant. Causes severe irritation. Severe lachrymator.
Fire Fighting:Extinguish: using carbon dioxide, dry chemical powder, or appropriate foam. Water spray: Wear self-contained breathing apparatus and protective clothing to prevent contact with skin and eyes.
Small spills/leaks:Cover with dry lime or soda ash, pick up, keep in a closed container, and hold for waste disposal. Ventilate area and wash spill site after material pickup is complete.
Incompatibilities:Strong oxidizing agents, Strong bases, Strong reducing agents.
Decomposition:Carbon monoxide, Carbon dioxide.

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